John Zeratsky was a designer in the tech industry has worked with hundreds of startups in his time at Google Ventures.  He’s also obsessed with redesigning time and thinking about what matters in life. Earlier this year he just got back from 18 months living on his boat sailing around Central America, which he wrote about in an article titled “What quitting my job to sail around central america taught me about fulfillment.”

John describes himself as “risk averse” but after being influenced by different perspectives on risk (including thoughts from the incredibly thoughtful Brian Koppelman) he realized that he could take smaller steps to test out a bigger leap.  So in advance of taking the trip, him and his wife avoided the trappings of lifestyle creep by saving 50% of their salaries and avoiding the urge to upgrade their apartment.  As a way to test whether they would like a longer sailing trip or not, they took smaller trips, going for a two week trip and a two month trip before heading out. This helped them learn about how they would feel and practice some of the skills they would need while living on the boat.

In this conversation we talk about:

  • Growing up in a small lake community
  • His love of sailing growing up
  • Why him and his wife change their mind on taking the trip in 2015
  • Rethinking convenience and comfort
  • What comforts are worth paying for
  • Belonging and community
  • How his relationship with money has changed
  • How him and his wife are structuring their life to work how they want
  • The one change that helps people be less addicted to their phones

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